Structures and physical properties of gaseous Metal cationized biological ions

European Journal of Mass Spectrometry

Volumn 18, Issue 2, 2012, Pages 235-250

  Burt, Michael B ^a   Fridgen, Travis D ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

Amino acids; DNA base; Electronic structure calculations; FT ICR; Gas phase; IRMPD sspectroscopy; Mass spectrometry; Metal cation; Solvation

Indexed keywords

AMINO ACIDS; BIOMOLECULES; DISSOCIATION; ELECTRONIC STRUCTURE; GASES; ISOMERS; MASS SPECTROMETERS; MASS SPECTROMETRY; METAL COMPLEXES; POSITIVE IONS; SOLVATION;

ELECTRONIC STRUCTURE CALCULATIONS; FT-ICR; GASPHASE; IRMPD SSPECTROSCOPY; METAL CATION;

METALS;

AMINO ACID; CATION; METAL; NUCLEOSIDE; NUCLEOTIDE; PROTEIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GAS; INFRARED SPECTROSCOPY; ISOMERISM; MASS SPECTROMETRY; METHODOLOGY;

AMINO ACIDS; CATIONS; GASES; ISOMERISM; MASS SPECTROMETRY; METALS; MODELS, MOLECULAR; NUCLEOSIDES; NUCLEOTIDES; PROTEINS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 84861998848     PISSN: 14690667     EISSN: None     Source Type: Journal    
DOI: 10.1255/ejms.1177     Document Type: Article

References (76)

1. L. McFail-Isom, C. C. Sines and L. D. Williams, "DNA structure: Cations in charge?", Curr. Opin. Struct. Biol. 9, 298 (1999). doi: 10.1016/S0959-440X (99) 80040-2
2. K. Rajabi, E. A. L. Gillis and T. D. Fridgen, "Structures of alkali metal ion-adenine complexes and hydrated complexes by IRMPD spectroscopy and electronic structure calculations", J. Phys. Chem. A 114, 3449 (2010). doi: 10.1021/jp9098683
3. 2+ (M = Cu, Pb) systems", Int. J. Mass Spectrom. 306, 27 (2011). doi: 10.1016/j.ijms.2011.05.018
4. N. Russo, M. Toscano and A. Grand, "Bond energies and attachments sites of sodium and potassium cations to DNA and RNA nucleic acid bases in the gas phase", J. Am. Chem. Soc. 123, 10272 (2001). doi: 10.1021/ja010660j (Pubitemid 32979776)
5. 2+ binding to all tautomers of adenine, cytosine and thymine and the eight most stable keto/enol tautomers of guanine: A correlated ab initio quantum chemical study", J. Phys. Chem. B 110, 14515 (2006). doi: 10.1021/jp062249u (Pubitemid 44188020)
6. A. M. Pyle, "Metal ions in the structure and function of RNA", J. Biol. Inorg. Chem. 7, 679 (2002). doi: 10.1007/s00775-002-0387-6 (Pubitemid 36056354)
7. V. N. Potaman and V. N. Soyfer, "Divalent metal cations upon coordination to the N7 of purines differentially stabilize the PyPuPu DNA triplex due to unequal Hoogsteen-type hydrogen bond enhancement", J. Biomol. Struct. Dyn. 11, 1035 (1994).
8. *poly (dG-dC) ", Biochemistry 23, 6159 (1984). doi: 10.1021/bi00320a041
9. T. D. Fridgen, "Infrared consequence spectroscopy of gaseous protonated and metal ion cationized complexes", Mass Spectrom. Rev. 28, 586 (2009). doi: 10.1002/mas.20224
10. N. C. Polfer and J. Oomens, "Vibrational spectroscopy of bare and solvated ionic complexes of biological relevance", Mass Spectrom. Rev. 28, 468 (2009). doi: 10.1002/mas.20215
11. P. Hajieva and C. Behl, "Antioxidants as a potential therapy against age-related neurodegenerative diseases: Amyloid beta toxicity and Alzheimer's disease", Curr. Pharm. Design 12, 699 (2006). doi: 10.2174/ 138161206775474297
12. S. Velez, N. G. Nair and V. P. Reddy, "Transition metal ion binding studies of carnosine and histidine: Biologically relevant antioxidants", Colloids Surf. B 66, 291 (2008). doi: 10.1016/j.colsurfb.2008.06.012
13. A. E. O. Fisher and D. P. Naughton, "Metal ion chelating peptides with superoxide dismutase activity", Biomed. Pharmacother. 59, 158 (2005). doi: 10.1016/j.biopha.2005.03.008 (Pubitemid 40603327)
14. A. Kamariotis, O. V. Boyarkin, S. R. Mercier, R. D. Beck, M. F. Bush, E. R. Williams and T. R. Rizzo, "Infrared spectroscopy of hydrated amino acids in the gas phase: Protonated and lithiated valine", J. Am. Chem. Soc. 128, 905 (2006). doi: 10.1021/ja056079v (Pubitemid 43153041)
15. + complexes using infrared multiple photon dissociation spectroscopy", J. Phys. Chem. B 115, 11506 (2011). doi: 10.1021/jp2068655
16. +-uracil complexes by IRMPD spectroscopy in the N-H/O-H stretching region", J. Phys. Chem. A 113, 824 (2009). doi: 10.1021/jp809993k
17. J. R. Eyler, "Infrared multiple dissociation spectroscopy of ions in Penning traps", Mass Spectrom. Rev. 28, 448 (2009). doi: 10.1002/mas.20217
18. + and the monosolvated water and methanol solvated species by infrared multiple-photon dissociation spectroscopy, energy-resolved collision-induced dissociation and electronic structure calculations", J. Phys. Chem. B 113, 14457 (2009). doi: 10.1021/jp905654v
19. C. G. Atkins, K. Rajabi, E. A. L. Gillis and T. D. Fridgen, "Infrared multiple photon dissociation spectra of protonand sodium ion-bound glycine dimers in the N-H and O-H stretching region", J. Phys. Chem. A 112, 10220 (2008). doi: 10.1021/jp805514b
20. +-adenine-thymine complex by IRMPD spectroscopy in the N-H/O-H stretching region", Int. J. Mass Spectrom. 297, 2 (2010). doi: 10.1016/j.ijms.2010.04.005
21. K. Rajabi and T. D. Fridgen, "Structures of aliphatic amino acid proton-bound dimers by infrared multiple photon dissociation spectroscopy in the 700-2000 cm-1 region", J. Phys. Chem. A 112, 23 (2008). doi: 10.1021/jp0736903 (Pubitemid 351169858)
22. K. Rajabi, K. Theel, A. E. L. Gillis, G. Beran and T. D. Fridgen, "The structure of the protonated adenine dimer by infrared multiple photon dissociation spectroscopy and electronic structure calculations", J. Phys. Chem. A 113, 8099 (2009). doi: 10.1021/jp9033062
23. + complexes by infrared multiple photon dissociation spectroscopy", Int. J. Mass Spectrom. 308, 167 (2011). doi: 10.1016/j.ijms.2011.04.003
24. D. Oepts, A. F. G. van der Meer and P. W. van Amersfoort, "The free electron laser user facility FELIX", Infrared Phys. Technol. 36, 297 (1995). doi: 10.1016/1350-4495 (94) 00074-U
25. J. M. Ortega, J. M. Berset, R. Chaput, F. Glotin, G. Humbert, D. Jaroszynski, P. Joly, B. Kergosien, J. Lesrel, O. Marcouillé, A. Peremans, R. Prazeres and A. Tadjeddine, "Activities of the CLIO infrared facility", Nucl. Instrum. Methods Phys. Res. Sect. A 375, 618 (1996). doi: 10.1016/0168-9002 (95) 01431-4
26. R. M. A. Heeren, A. J. Kleinnijenhuis, L. A. McDonnell and T. H. Mize, "A mini-review of mass spectrometry using high-performance FTICR-MS methods", Anal. Bioanal. Chem. 378, 1048 (2004). doi: 10.1007/s00216-003- 2446-4 (Pubitemid 40902519)
27. R. C. Dunbar, "BIRD (blackbody infrared radiative dissociation): Evolution, principles and applications", Mass Spectrom. Rev. 23, 127 (2004). doi: 10.1002/mas.10074
28. K. Rajabi, M. L. Easterling and T. D. Fridgen, "Solvation of electrosprayed ions in the accumulation/collision hexapole of a hybrid Q-FTMS", J. Am. Soc. Mass Spectrom. 20, 411 (2009). doi: 10.1016/j.jasms.2008.10.023
29. J.-Y. Salpin, S. Guillaumont, J. Tortajada, L. MacAleese, J. Lemaire and P. Maître, "Infrared spectra of protonated uracil, thymine and cytosine", ChemPhysChem 8, 2235 (2007). doi: 10.1002/cphc.200700284
30. J. M. Bakker, J.-Y. Salpin and P. Maître, "Tautomerism of cytosine probed by gas phase IR spectroscopy", Int. J. Mass Spectrom. 283, 214 (2009). doi: 10.1016/j. ijms.2009.03.014
31. M. T. Rodgers and P. B. Armentrout, "Noncovalent interactions of nucleic acid bases (uracil, thymine and adenine) with alkali metal ions. Threshold collisioninduced dissociation and theoretical studies", J. Am. Chem. Soc. 122, 8548 (2000). doi: 10.1021/ja001638d
32. M. Hanus, M. Kabelác., J. Rejnek, F. Ryjáček and P. Hobza, "Correlated ab initio study of nucleic acid bases and their tautomers in the gas phase, in a microhydrated environment and in aqueous solution. Part 3. adenine", J. Phys. Chem. B 108, 2087 (2004). doi: 10.1021/jp036090m
33. N. Russo, M. Toscano and A. Grand, "Lithium affinity for DNA and RNA nucleobases. The role of theoretical information in the elucidation of the mass spectrometry data", J. Phys. Chem. B 105, 4735 (2001). doi: 10.1021/jp004583a (Pubitemid 35375173)
34. 2+ ions on the hydrogen bonds of the Watson-Crick base pairs", Biopolymers 29, 757 (1990). doi: 10.1002/bip. 360290410
35. 2+): Nonempirical ab initio calculations on structures, energies and nonadditivity of the interaction", J. Phys. Chem. B 101, 9670 (1997). doi: 10.1021/jp963753+
36. G. M. Krishnan and O. Kühn, "Identifying adenine-thymine base pairing by anharmonic analysis of the hydrogenbonded NH stretching vibrations", Chem. Phys. Lett. 435, 132 (2007). doi: 10.1016/j.cplett.2006. 12.072 (Pubitemid 46148871)
37. 2+ complexes in the gas phase", ChemPhysChem 8, 181 (2007). doi: 10.1002/cphc.200600399
38. + in the gas phase", ChemPhysChem 13, 588 (2012). doi: 10.1002/cphc.201100661
39. S. Guillaumont, J. Tortajada, J.-Y. Salpin and A. M. Lamsabhi, "Experimental and computational study of the gas-phase interactions between lead (II) ions and two pyrimidic nucleobases: uracil and thymine", Int. J. Mass Spectrom. 243, 279 (2005). doi: 10.1016/j.ijms.2005.03.011 (Pubitemid 40653313)
40. 2+ with uracil and its thio derivatives in the gas phase", Org. Biomol. Chem. 6, 3695 (2008). doi: 10.1039/b810418b
41. + complexes (M = Zn, Cu, Ni, Co, Fe, Mn, Cd, Pd, Mg, Ca, Sr, Ba and Pb", ChemPhysChem 13, 1507 (2012). doi: 10.1002/cphc.201200015
42. J. T. Davis, "G-quartets 40 years later: From 5′-GMP to molecular biology and supramolecular chemistry", Angew. Chem. Int. Ed. 43, 668 (2004). doi: 10.1002/anie.200300589 (Pubitemid 38197045)
43. R. H. Shafer and I. Smirnov, "Biological aspects of DNA/RNA quadruplexes", Biopolymers 56, 209 (2000). doi: 10.1002/1097-0282 (2000/2001) 56:3<209::AID-BIP10018>3.0. CO;2-Y
44. S. Katayama, G. Shiota, M. Oshimura and H. Kawasaki, "Clinical usefulness of telomerase activity and telomere length in the preoperative diagnosis of gastric and colorectal cancer", J. Cancer Res. Clin. Oncol. 125, 405 (1999). doi: 10.1007/s004320050294 (Pubitemid 29287499)
45. C. Cheong and P. B. Moore, "Solution structure of an unusually stable RNA tetraplex containing G-and U-quartet structures", Biochemistry 31, 8406 (1992). doi: 10.1021/bi00151a003
46. K. J. Koch, T. Aggerholm, S. C. Nanita and R. G. Cooks, "Clustering of nucleobases with alkali metals studied by electrospray ionization tandem mass spectrometry: implications for mechanisms of multistrand DNA stabilization", J. Mass Spectrom. 37, 676 (2002). doi: 10.1002/jms.326 (Pubitemid 34830805)
47. T. Aggerholm, S. C. Nanita, K. J. Koch and R. G. Cooks, "Clustering of nucleosides in the presence of alkali metals: Biologically relevant quartets of guanosine, deoxyguanosine and uridine observed by ESI-MS/MS", J. Mass Spectrom. 38, 87 (2003). doi: 10.1002/jms.405 (Pubitemid 36157761)
48. E.-L. Zins, S. Rochut and C. Pepe, "Formation of complexes between uracil and calcium ions: An ESI/MS/MS study in combination with theoretical calculations", J. Mass Spectrom. 44, 813 (2009). doi: 10.1002/jms.1561
49. E. A. L. Gillis, Structures and Energetics of Non-Covalently Bound Gaseous Ions by Infrared Photodissociation. PhD dissertation, Memorial University of Newfoundland, St. John's, Newfoundland, Canada (2011).
50. 2+ clusters (n = 14-4) in the gas phase", Phys. Chem. Chem. Phys. 14, 3304 (2011). doi: 10.1039/c1cp22984b
51. C. J. Chapo, J. B. Paul, R. A. Provencal, K. Roth and R. J. Saykally, "Is arginine zwitterionic or neutral in the gas phase? Results from IR cavity ringdown spectroscopy", J. Am. Chem. Soc. 120, 12956 (1998). doi: 10.1021/ja982991a (Pubitemid 29013848)
52. R. C. Dunbar, N. C. Polfer and J. Oomens, "Gas-phase zwitterion stabilization by a metal dication", J. Am. Chem. Soc. 129, 14562 (2007). doi: 10.1021/ja076131i (Pubitemid 350207862)
53. B. M. Rode, "Peptides and the origin of life", Peptides 20, 773 (1999). doi: 10.1016/S0196-9781 (99) 00062-5
54. J. C. Ma and D. A. Dougherty, "The cation-pi interaction", Chem. Rev. 97, 1303 (1997). doi: 10.1021/cr9603744
55. P. B. Armentrout, M. T. Rodgers, J. Oomens and J. D. Steill, "Infrared multiphoton dissociation spectroscopy of cationized serine: Effects of alkali-metal cation size on gas-phase conformation", J. Phys. Chem. A 112, 2248 (2008). doi: 10.1021/jp710885a
56. 2+) and glycine", J. Phys. Chem. B 110, 24666 (2006). doi: 10.1021/jp0645972 (Pubitemid 46065771)
57. M. K. Drayß, P. B. Armentrout, J. Oomens and M. Schäfer, "IR spectroscopy of cationized aliphatic amino acids: Stability of charge-solvated structure increases with metal cation size", Int. J. Mass Spectrom. 297, 18 (2010). doi: 10.1016/j.ijms.2010.04.010
58. 2+ (M = Be, Mg, Ca, Sr, Ba), in the gas phase: Intrinsic effect of cation size on zwitterion stability", J. Phys. Chem. A 104, 9793 (2000). doi: 10.1021/jp002970e
59. 2+ with glycine. A theoretical study", J. Phys. Chem. A 109, 224 (2005). doi: 10.1021/jp047590y (Pubitemid 40134467)
60. R. M. Moision and P. B. Armentrout, "Experimental and theoretical dissection of sodium cation/glycine interactions", J. Phys. Chem. A 106, 10350 (2002). doi: 10.1021/jp0216373 (Pubitemid 35313814)
61. C. Kapota, J. Lemaire, P. Maître and G. Ohanessian, "Vibrational signature of charge solvation vs salt bridge isomers of sodiated amino acids in the gas phase", J. Am. Chem. Soc. 126, 1836 (2004). doi: 10.1021/ja036932v
62. M. F. Bush, J. Oomens, R. J. Saykally and E. R. Williams, "Effects of alkaline earth metal ion complexation on amino acid zwitterion stability: Results from infrared action spectroscopy", J. Am. Chem. Soc. 130, 6463 (2008). doi: 10.1021/ja711343q (Pubitemid 351706109)
63. M. W. Forbes, M. F. Bush, N. C. Polfer, J. Oomens, R. C. Dunbar, E. R. Williams and R. A. Jockusch, "Infrared spectroscopy of arginine cation complexes: Direct observation of gas-phase zwitterions", J. Phys. Chem. A 111, 11759 (2007). doi: 10.1021/jp074859f (Pubitemid 350247195)
64. W. D. Price, R. A. Jockusch and E. R. Williams, "Is arginine a zwitterion in the gas phase?", J. Am. Chem. Soc. 119, 11988 (1997). doi: 10.1021/ja9711627 (Pubitemid 28012766)
65. +, M = H, Li, Na, K, Rb and Cs) in the gas phase: Further evidence for zwitterionic arginine", J. Phys. Chem. A 103, 9266 (1999). doi: 10.1021/jp9931307
66. M. F. Bush, J. T. O'Brien, J. S. Prell, R. J. Saykally and E. R. Williams, "Infrared spectroscopy of cationized arginine in the gas phase: Direct evidence for the transition from nonzwitterionic to zwitterionic structure", J. Am. Chem. Soc. 129, 1612 (2007). doi: 10.1021/ja066335j
67. M. F. Bush, M. W. Forbes, R. A. Jockusch, J. Oomens, N. C. Polfer, R. J. Saykally and E. R. Williams, "Infrared spectroscopy of cationized lysine and e-N-methyllysine in the gas phase: Effects of alkali-metal ion size and proton affinity on zwitterion stability", J. Phys. Chem. A 111, 7753 (2007). doi: 10.1021/jp071902q (Pubitemid 47310914)
68. N. C. Polfer, J. Oomens and R. C. Dunbar, "IRMPD spectroscopy of metal-ion/tryptophan complexes", Phys. Chem. Chem. Phys. 8, 2744 (2006). doi: 10.1039/b603665a
69. L. Patrick, "Lead toxicity, A review of the literature. Part I: Exposure, evaluation and treatment", Altern. Med. Rev. 11, 2 (2006).
70. F. Rogalewicz, Y. Hoppilliard and G. Ohanessian, "Structures and fragmentations of zinc (II) complexes of amino acids in the gas phase. I. Electrosprayed ions which are structurally different from their liquid phase precursors", Int. J. Mass Spectrom. 201, 307 (2000). doi: 10.1016/S1387-3806 (00) 00226-8
71. Y. Hoppilliard, F. Rogalewicz and G. Ohanessian, "Structures and fragmentations of zinc (II) complexes of amino acids in the gas phase. II. Decompositions of glycine-Zn (II) complexes", Int. J. Mass Spectrom. 204, 267 (2000). doi: 10.1016/S1387-3806 (00) 00358-4
72. F. Rogalewicz, Y. Hoppilliard and G. Ohanessian, "Structures and fragmentations of zinc (II) complexes of amino acids in the gas phase. III. Rearrangement versus desolvation in the electrospray formation of the glycine-zinc complex", Int. J. Mass Spectrom. 206, 45 (2001). doi: 10.1016/S1387-3806 (00) 00383-3
73. F. Rogalewicz, Y. Hoppilliard and G. Ohanessian, "Structures and fragmentations of zinc (II) complexes of amino acids in the gas phase. IV. Solvent effect on the structure of electrosprayed ions", Int. J. Mass Spectrom. 227, 439 (2003). doi: 10.1016/S1387-3806 (03) 00103-9
74. 2+", Int. J. Mass Spectrom. 308, 330 (2011). doi: 10.1016/j.ijms.2011.08.018
75. N. C. Polfer, J. Oomens, S. Suhai and B. Paizs, "Infrared spectroscopy and theoretical studies on gas-phase protonated leu-enkephalin and its fragments: direct experimental evidence for the mobile proton", J. Am. Chem. Soc. 129, 5887 (2007). doi: 10.1021/ja068014d (Pubitemid 46748493)
76. V. Gabelica, F. Rosu, E. De Pauw, J. Lemaire, J.-C. Gillet, J.-C. Poully, F. Lecomte, G. Grégoire, J.-P. Schermann and C. Desfrançois, "Infrared signature of DNA G-quadruplexes in the gas phase", J. Am. Chem. Soc. 130, 1810 (2008). doi: 10.1021/ja077321w (Pubitemid 351238620)